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Unit 2: Carbon Compounds (a)Fuels (i) Combustion A fuel is a chemical which is burned to produce energy. Combustion is another word for burning. When a substance burns it reacts with oxygen. The chemical compounds which are found in oil and natural gas are mainly hydrocarbons. A hydrocarbon is a compound which contains hydrogen and carbon only. Hydrocarbons burn in a plentiful supply of air to produce carbon dioxide and water. The test for carbon dioxide is that it turns lime water milky. Carbon, and carbon monoxide, a poisonous gas, are produced when the hydrocarbons burn in a supply of oxygen which is insufficient for complete combustion. Nitrogen and oxygen from the air react inside a petrol engine to form nitrogen oxides which are poisonous gases. The burning of some fuels releases sulphur dioxide, a poisonous gas, into the atmosphere. Soot particles produced by the incomplete combustion of diesel are harmful. Air pollution from the combustion of hydrocarbons can be reduced by the use of catalytic converters which speed up the conversion of pollutant gases to harmless gases. (ii) Fractional distillation Crude oil is a mixture of chemical compounds, mainly hydrocarbons. Fractional distillation is the process used to separate crude oil into fractions according to the boiling points of the components of the fractions. A fraction is a group of hydrocarbons with boiling points within a given range. Ease of evaporation, viscosity, flammability and boiling point range of the fractions are properties related to molecular sizes of the molecules within the fractions. The uses of the fractions are related to the ease of evaporation, viscosity, flammability and boiling point range of the fractions. b) Nomenclature and structural formulae (i) Hydrocarbons The alkanes are a subset of the set of hydrocarbons. An alkane can be identified from the ‘-ane’ ending. Straight-chain alkanes can be named from molecular formulae, shortened and full structural formulae (only C1 to C8). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the names of straight-chain alkanes (only C1 to C8). Branched-chain alkanes can be systematically named from shortened and full structural formulae (only C4 to C8). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the systematic names of branched-chain alkanes (only C4 to C8). The alkenes are a subset of the set of hydrocarbons. An alkene can be identified from the carbon to carbon double bond and the ‘-ene’ ending. Straight-chain alkenes can be named, incorporating the position of the double bond, from shortened and full structural formulae (only C 2 to C8). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the names of alkenes (only C2 to C8). The cycloalkanes are a subset of the set of hydrocarbons. A cycloalkane can be identified from the name. Cycloalkanes can be named from molecular formulae, shortened and full structural formulae (only C3 to C8; isomers are not required, eg only cyclohexane is expected, not methylcyclopentane). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the names of cycloalkanes (only C 3 to C8). A homologous series is a set of compounds with the same general formula and similar chemical properties. (ii) Isomers Isomers are compounds with the same molecular formulae but different structural formulae. Isomers can be drawn for given molecular formulae, shortened and full structural formulae. The alkenes are a subset of the set of hydrocarbons. An alkene can be identified from the carbon to carbon double bond and the ‘-ene’ ending. Straight-chain alkenes can be named, incorporating the position of the double bond, from shortened and full structural formulae (only C2 to C8). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the names of alkenes (only C2 to C8). The cycloalkanes are a subset of the set of hydrocarbons. A cycloalkane can be identified from the name. Cycloalkanes can be named from molecular formulae, shortened and full structural formulae (only C3 to C8; isomers are not required, eg only cyclohexane is expected, not methylcyclopentane). Molecular formulae can be written and shortened and full structural formulae can be drawn, given the names of cycloalkanes (only C 3 to C8). A homologous series is a set of compounds with the same general formula and similar chemical properties. (ii) Isomers Isomers are compounds with the same molecular formulae but different structural formulae. Isomers can be drawn for given molecular formulae, shortened and full structural formulae. c) Reactions of carbon compounds (i) Addition reactions The alkanes and the cycloalkanes are saturated hydrocarbons. Saturated hydrocarbons contain only carbon to carbon single covalent bonds. The alkenes are unsaturated hydrocarbons. Unsaturated hydrocarbons contain at least one carbon to carbon double covalent bond. It is possible to distinguish an unsaturated hydrocarbon from a saturated hydrocarbon using bromine solution. An alkene reacts with hydrogen to form the corresponding alkane. The reactions of an alkene with bromine, hydrogen and water are addition reactions. (ii) Cracking Fractional distillation of crude oil yields more long-chain hydrocarbons than are useful for present-day industrial purposes. Cracking is an industrial method for producing a mixture of smaller, more useful molecules, some of which are unsaturated. The catalyst allows the reaction to take place at a lower temperature. Cracking can be carried out in the laboratory using an aluminium oxide or silicate catalyst. (iii) Ethanol Ethanol, for alcoholic drinks, can be made by fermentation of glucose derived from any fruit or vegetable. An enzyme in yeast acts as a catalyst for the reaction. There is a limit to the ethanol concentration of fermentation products. Distillation is a method of increasing the ethanol concentration of fermentation products in the manufacture of ‘spirit’ drinks. Alcoholic drinks, if taken in excess, can have damaging affects to health and mind. To meet market demand ethanol is made by means other than fermentation. Industrial ethanol is manufactured by the catalytic hydration of ethene. Ethanol can be converted to ethene by dehydration. Ethanol, mixed with petrol, can be used as a fuel for cars. The ethanol is obtained from sugar cane, a renewable source of energy. (iv) Making and breaking esters Esters are formed by the condensation reaction between a carboxylic acid and an alcohol. In a condensation reaction, the molecules join together by the reaction of the functional groups to make water. The ester link is formed by the reaction of a hydroxyl group with a carboxyl group. The parent carboxylic acid and the parent alcohol can be obtained by hydrolysis of an ester. The formation and hydrolysis of an ester is a reversible reaction. d) Plastics and synthetic fibres (i) Uses Synthetic materials are made by the chemical industry. Most plastics and synthetic fibres are made from chemicals derived from oil. Examples of plastics include polythene, polystyrene, perspex, PVC, nylon, bakelite, formica and silicones. Kevlar, which is very strong, and poly(ethenol), which readily dissolves in water, are recently developed plastics. The everyday uses of plastics are related to their properties. Examples of synthetic fibres include polyesters, eg Terylene, and nylon. For some uses, synthetic materials have advantages over natural materials and vice versa. Biopol is a recently developed degradable plastic. Most plastics are not biodegradable and their low density and durability can cause environmental problems. Some plastics burn or smoulder to give off toxic fumes, including carbon monoxide. The toxic gases given off during burning or smouldering can be related to the elements present in the plastic. Plastics can be either thermoplastic or thermosetting. A thermoplastic is one which can be reshaped on heating. A thermosetting plastic cannot be reshaped by heating. (ii) Addition polymerisation Plastics are made up of long chain molecules called polymers. Polymer molecules are made from many small molecules called monomers. Addition polymers are made from small unsaturated molecules produced by cracking by a process called addition polymerisation. The small unsaturated molecules join together by the opening of the carbon to carbon double bond. The name of the addition polymer is related to the name of the monomer. The repeating unit or the structure of an addition polymer can be drawn given the monomer structure and vice versa. (iii) Condensation polymerisation Condensation polymers are made from monomers with two functional groups per molecule. The repeating unit or the structure of a condensation polymer can be drawn given the monomer structures and vice versa. Polyesters are examples of condensation polymers. An amine can be identified from the functional group. Polyamides are examples of condensation polymers. The amide link is formed by the reaction of an amine group with a carboxyl group. e) Natural products (i) Carbohydrates Carbohydrates form an important class of food made by plants. Carbohydrates supply the body with energy. Carbohydrates are compounds which contain carbon, hydrogen and oxygen with the hydrogen and oxygen in the ratio of two to one. Carbohydrates can be divided into sugars and starches. Examples of sugars include glucose, fructose, maltose and sucrose (table sugar). Most sugars can be detected by the Benedict’s test; sucrose is an exception. Starch can be distinguished from other carbohydrates by the iodine test. Sugars are carbohydrates with small molecules. Starch is a natural condensation polymer made of many glucose molecules linked together. Plants convert the glucose into starch for storing energy. During digestion starch is hydrolysed to glucose which is carried by the blood stream to body cells. Starch can be hydrolysed by acid and by enzymes. Body enzymes function best at body temperature and are destroyed at higher temperature. (ii) Proteins Proteins form an important class of food made by plants. Proteins are the major structural materials of animal tissue and are involved in the maintenance and regulation of life processes and include enzymes, many hormones, eg insulin and haemoglobin. Proteins are condensation polymers made of many amino acid molecules linked together. The structure of a section of protein is based on the constituent amino acids. Condensation of amino acids produces the peptide (amide) link. The peptide link is formed by the reaction of an amine group with a carboxyl group. Proteins specific to the body’s needs are built up within the body. During digestion enzyme hydrolysis of dietary proteins produces amino acids. The structural formulae of amino acids obtained from the hydrolysis of proteins can be identified from the structure of a section of the protein. (iii) Fats and oils Natural fats and oils can be classified according to their origin as animal, vegetable or marine. The lower melting points of oils compared to those of fats is related to the higher unsaturation of oil molecules. The conversion of oils into hardened fats involves the partial removal of unsaturation by addition of hydrogen. Fats and oils in the diet supply the body with energy and are a more concentrated source of energy than carbohydrates. Fats and oils are esters. The hydrolysis of fats and oils produces fatty acids and glycerol in the ratio of three moles of fatty acid to one mole of glycerol. Fatty acids are saturated or unsaturated straight chain carboxylic acids, usually with long chains of carbon atoms.